1-(4-chlorophenylamino)-1-phenylpentan-3-one | 137351-26-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-chlorophenylamino)-1-phenylpentan-3-one
• 英文别名: 1-phenyl-1-(4-chlorophenylamino)-3-pentanone；1-(4-Chloroanilino)-1-phenylpentan-3-one；1-(4-chloroanilino)-1-phenylpentan-3-one
• CAS: 137351-26-9
• 化学式: C₁₇H₁₈ClNO
• 分子量: 287.789
• InChiKey: KOHJPRKQLOBKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenylamino)-1-phenylpentan-3-one 在 间氯过氧苯甲酸 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Radical transformations of some N-alkylanilines by their oxidation with different agents: an EPR study

  摘要：

  N-Alkylanilines X-NH-Ph (Ph = substituted phenyl ring) with two different types of alkyl substituent X [X = C2H5-CO-CH2CH(Ph), X = CH3, C2H5, CH(CH3)(2), CH2C6H5] were oxidized using different agents. While oxidation with 3-chloroperbenzoic acid leads to production of the corresponding aminoxyl radicals X-NOaEuro cent-Ph, it was confirmed that application of PbO2 resulted in the formation of aminyl radicals X-N-aEuro cent-Ph, as indirectly proved by the spin-trapping method. Contrary to those transformations, with employment of either Pb(OAc)(4) or t-BuO (2) (aEuro cent) radical, reactions taking place on the alkyl substituent were also observed.

  DOI：

  10.1007/s00706-012-0874-6
• 作为产物：
  描述：

  N-亚苄基-4-氯苯胺 、 丁酮 在 2,6-二叔丁基吡啶 、 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以83%的产率得到1-(4-chlorophenylamino)-1-phenylpentan-3-one
  参考文献：
  名称：

  持久性阳离子阳离子盐诱导的曼尼希反应合成β-氨基酮和构建高取代的4-哌啶酮

  摘要：

  研究了持久性自由基阳离子盐诱导的亚胺和酮的曼尼希反应，并合成了一系列曼尼希碱，即β-氨基酮。在串联过程中实现了形成4-哌啶酮骨架的新型环化反应。可以将反应合理化为各种证据支持的自由基阳离子过程。

  DOI：

  10.1021/ol9027978

文献信息

• The Mannich Reaction of Butanone, Aromatic Aldehydes and Aromatic Amines
  作者：Yi Lin、Zou Junhua、Lei Huangshu、He Qilin

  DOI：10.1080/00397919108019818

  日期：1991.10

  Abstract Under the catalysis of small amount of concentrated hydrochloric acid, the Mannich reaction of butanone, aromatic aldehydes and aromatic amines can be carried out directly at 0–20°C. Twelve corresponding Mannich bases (1), 1-aryl-1-arylamino-3-pentanones, were prepared in high yields.

  摘要 在少量浓盐酸的催化下，丁酮、芳香醛和芳香胺的曼尼希反应可在0～20℃直接进行。以高产率制备了十二种相应的曼尼希碱 (1)，即 1-芳基-1-芳基氨基-3-戊酮。
• Synthesis of β-Aminoketones and Construction of Highly Substituted 4-Piperidones by Mannich Reaction Induced by Persistent Radical Cation Salts
  作者：Xiao-Dong Jia、Xiao-E Wang、Cai-Xia Yang、Cong-De Huo、Wen-Juan Wang、Yan Ren、Xi-Cun Wang

  DOI：10.1021/ol9027978

  日期：2010.2.19

  A Mannich reaction of imines and ketones induced by persistent radical cation salts was investigated, and a series of Mannich bases, β-aminoketones, were synthesized. A novel cyclization to form the 4-piperidone skeleton was achieved in a tandem process. The reaction can be rationalized as a radical cation process supported by various evidence.

  研究了持久性自由基阳离子盐诱导的亚胺和酮的曼尼希反应，并合成了一系列曼尼希碱，即β-氨基酮。在串联过程中实现了形成4-哌啶酮骨架的新型环化反应。可以将反应合理化为各种证据支持的自由基阳离子过程。
• Radical transformations of some N-alkylanilines by their oxidation with different agents: an EPR study
  作者：Lenka Šafaříková、Ladislav Omelka、Petr Majzlík、Jan Světlík

  DOI：10.1007/s00706-012-0874-6

  日期：2013.2

  N-Alkylanilines X-NH-Ph (Ph = substituted phenyl ring) with two different types of alkyl substituent X [X = C2H5-CO-CH2CH(Ph), X = CH3, C2H5, CH(CH3)(2), CH2C6H5] were oxidized using different agents. While oxidation with 3-chloroperbenzoic acid leads to production of the corresponding aminoxyl radicals X-NOaEuro cent-Ph, it was confirmed that application of PbO2 resulted in the formation of aminyl radicals X-N-aEuro cent-Ph, as indirectly proved by the spin-trapping method. Contrary to those transformations, with employment of either Pb(OAc)(4) or t-BuO (2) (aEuro cent) radical, reactions taking place on the alkyl substituent were also observed.